Hydrochloric Acid → p-Toluenesulfinic acid

To a round bottom flask was added sodium 4-methylbenzenesulfinate (25 g, 140 mmol), MTBE (40 mL) and water (80 mL). To the reaction mixture was added concentrated HCl (12.7 mL, 154 mmol) dropwise via addition funnel over about 15 min. The resulting layers were separated and the aqueous layer extracted with MTBE (2×50 mL). The organic layers were combined and dried with MgSO4, filtered and concentrated in vacuo. The resulting solid was triturated with heptane, filtered, and dried under vacuum to provide the title compound (21.5 g, 98%). LC/MS (Table 1, Method a) Rt=1.12 min; MS m/z: 155.1 (M−H)−.

1. additiondropwise via addition funnel over about 15 min
2. customThe resulting layers were separated
3. extractionthe aqueous layer extracted with MTBE (2×50 mL)
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting solid was triturated with heptane
8. filtrationfiltered
9. customdried under vacuum

ORD record

ord-52e4cc14a0eb4c5088927b7abf3e63dd

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188083B2